Set the event's Start Time earlier, e.g. 5 seconds or whatever time you find approproate
I just watched another example of this at 8 this morning. In this particular case, it had absolutely nothing to do with time compression. There were 17 seconds left before the hour, and no suitable sweeper was available. Yes, a suitable sweeper would have been great, but there wasn't one.
The playlist for the 8:00 event had already been generated at 7:57:02. At 7:59:43, radio boss started another song. The event's content was inserted at 8:00, but then waited behind that song until 8:03:33. So rather than allowing the event to begin 17 seconds early, it began 3 minutes and 33 seconds late.
This is a situation where the five second suggestion wouldn't solve the problem. The song would already be playing before the event was inserted, and the maximum wait option would then interrupt it at 8:00. I would rather have the already generated content follow naturally.
Looking back over the material leading up to this, the raw files totaled about 60 minutes and 29 seconds, but playback moved through them in 59 minutes and 32 seconds. I'm not attributing that difference to time compression. The point is that the file lengths and the time actually occupied in the hour are different, and sometimes there isn't a sweeper available to make up what's left.
That's why I keep coming back to making the generated content available before the event's scheduled time. Radio boss already had the next program ready. I wanted it to use that content when the previous material finished, rather than start another song.
For transparency, I used AI to help gather the timestamps and file durations through the RadioBOSS API and help put this response together. The behavior I'm describing is something I watched happen, and the figures come from RadioBOSS itself.